iwon™ podcast with Michael J Thomas

AI Skills and Future of Work - Building a Gold Standard That Doesn't Exist (Yet) | Aatish Thakerar | iwon™ podcast Ep. 9.

AI is moving at a rapid pace. Most education institutions, schools and companies cannot keep up with it. While technology continues to reshape industries, careers, and the future of work, many education systems are still trying to figure out how to respond. In this 9th episode of the iwon™ podcast, Michael J. Thomas sits down with Aatish Thakerar, Co-Founder of Pedagogue, to discuss one of the biggest challenges facing education today: preparing the next generation for a world powered by AI. A former British Army Reservist, engineering leader, and startup founder, Aatish brings a unique perspective on technology, learning, leadership, and the realities of building a business in one of the fastest-moving industries on the planet. Before launching Pedagogue, Aatish founded and exited an AI startup before spending four years helping scale Climate X through multiple stages of growth. Along the way, he learnt first-hand what works, what doesn't, and why timing, distribution, and economics often matter more than founders realise. Together, Michael and Aatish explore AI literacy, startup lessons, product-market fit, education reform, future careers, large language models, agentic AI, and why schools must rethink what "elite education" means in the age of artificial intelligence. If you're a founder, educator, parent, student, or simply curious about where AI is taking us next, this conversation is packed with practical insights and thought-provoking ideas. IN THIS EPISODE • Why AI is advancing faster than most education systems can adapt • What "elite education" looks like in the age of AI • Lessons from building and exiting an AI startup • Why timing, distribution, and economics matter in startup success • Product-market fit and knowing when to pivot • Why education became Pedagogue's focus • The future of work and the skills students need most • The opportunities and risks of large language models • Agentic AI, automation, and what comes next • Why founders should avoid outsourcing all of their thinking to technology • Leadership lessons from the British Army • Why human creativity still matters in an AI-powered future CHAPTERS 00:00 AI Is Moving Faster Than Education 00:36 Welcome to the iwon™ podcast 01:40 Building and Selling an AI Startup 04:18 Startup Lessons, Risk, and Luck 07:07 The UK vs Silicon Valley 12:00 Product Market Fit and Enterprise Challenges 14:14 The Palantir Problem 16:17 Why Education Became the Focus 17:34 What Is Elite Education Today? 20:24 Why Schools Must Teach AI 23:16 Why AI Could Increase Inequality 25:49 Why Not Start With Government Contracts 31:31 Is Pedagogue the Right Solution? 34:00 The AI Boom and Startup Reality 36:52 Why Most People Misunderstand AI 38:00 Teaching AI Without Platform Bias 41:08 Agentic AI and the Future 46:00 How Founders Avoid Overengineering 50:41 Leadership Lessons Beyond Technology 54:28 Think Long Term and Compound 56:00 Are We Outsourcing Thinking? 57:50 Unknown Unknowns and Human Creativity 58:52 Final Thoughts CONNECT WITH AATISH THAKERAR LinkedIn: https://www.linkedin.com/in/aatish-thakerar/ [https://www.linkedin.com/in/aatish-thakerar/] Pedagogue: https://pedagogue.io/ [https://pedagogue.io/] Pedagogue on LinkedIn: https://www.linkedin.com/company/pedagogue-schools/ [https://www.linkedin.com/company/pedagogue-schools/] CONNECT WITH MICHAEL J. THOMAS LinkedIn: https://www.linkedin.com/in/realmjt-in/ [https://www.linkedin.com/in/realmjt-in/] STUCK WHERE YOU ARE WITH YOUR SAAS OR B2B TECH PRODUCT? Michael and the team at DARWIN™ Works help founders simplify their message, sharpen their positioning, and accelerate growth. Find out more: https://darwinworks.com/ [https://darwinworks.com/] LEARN MORE ABOUT THE IWON™ PODCAST Website: https://www.iwonpodcast.com [https://www.iwonpodcast.com/] LinkedIn: https://linkedin.com/company/iwon-podcast [https://linkedin.com/company/iwon-podcast] Success isn't overnight. That's why we tell the real stories. Takeaways: * Artificial intelligence is advancing rapidly, while educational systems struggle to keep pace with these developments. * The incorporation of AI education in countries like China begins at a remarkably young age, highlighting deficits in the UK and US educational frameworks. * The role of schools extends beyond traditional education; they must prepare students for the future of work, integrating technology into their curriculums. * Founders must navigate the complexities of funding and commercial viability, particularly in the fluctuating landscape of AI and technology startups. Companies mentioned in this episode: * Pedagogue * Climatex * Palantir * Claude * Grok * Base44 * Replit And many more. Disclaimer: The views expressed in this podcast are those of the individual speakers and do not necessarily reflect the views of the producers or associated organisations. This podcast is provided for informational and entertainment purposes only and should not be considered financial, legal, or professional advice. Trademarks and Copyright: The IWON™ Podcast is produced by DARWIN™ Works, a trading name of BlueEyed Digital Marketing Ltd. IWON™ and DARWIN™ are registered trademarks. All content is copyright © BlueEyed Digital Marketing Ltd 2026.

The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8

Instagram wasn't an overnight success. Facebook required enormous funding. Most success stories take years. Most people see success and assume it happened quickly. Elizabeth Dodson knows better. What does it take to build a software company for 14 years without giving up? What looks like an overnight success story is actually the result of decades of learning, one successful software exit, countless pivots, thousands of conversations, and 14 years building HomeZada into a platform helping homeowners manage more than 100,000 properties. In this episode of the iwon™ podcast, Michael J. Thomas sits down with Elizabeth Dodson, Co-Founder of HomeZada, to discuss the realities of building a category-defining software company, creating strategic partnerships, navigating growth, and why success rarely happens as quickly as people think. Before HomeZada, Elizabeth helped grow and eventually sell Meridian Systems, a leading commercial construction project management software company. But it was a simple homeowner problem that sparked her next venture. After a costly hot water heater failure, she began searching for a way to manage home maintenance, inventories, warranties, and important property information. Despite the existence of sophisticated software used to build stadiums and skyscrapers, she couldn't find a solution designed for homeowners. So she decided to build one. In this conversation, Elizabeth shares the realities of creating an entirely new software category, the lessons learned from scaling multiple companies, and why persistence matters more than most founders realise. IN THIS EPISODE • How HomeZada was born from a personal frustration • Why founders should hire people smarter than themselves • The importance of contracts, negotiation, and protecting your interests • Building strategic partnerships that create value for everyone involved • How A/B testing and customer language transformed HomeZada's growth • The challenge of educating a market when your category doesn't exist yet • Why technical founders often underestimate marketing • The truth about "overnight success" • Protecting customer data and maintaining trust • Setting boundaries and avoiding founder burnout • Why persistence matters more than most people realise CHAPTERS 00:00 Why Most Startups Fail 00:36 Welcome to the iwon™ podcast 01:48 The Problem That Led to HomeZada 04:18 The Hidden Cost of Homeownership 05:39 The Hot Water Heater That Changed Everything 07:51 Searching for a Better Solution 11:53 Lessons From Building and Selling Meridian Systems 14:30 Contracts, Negotiation, and Protecting Yourself 19:59 Why You Should Hire People Smarter Than You 23:53 Learning an Entirely New Market 30:10 The Challenge of Creating a New Software Category 31:55 A/B Testing, Messaging, and Finding What Works 35:54 Handling Naysayers and Unhelpful Praise 39:31 Finding the Right Customer 42:08 Why HomeZada Pivoted to Busy Professionals 42:49 Don't Quit Too Soon 43:40 Starting Again With a Blank Whiteboard 44:26 Playing the Long Game 45:34 The Growth Mindset Advantage 46:55 The Myth of Overnight Success 50:46 Building Something You're Proud Of 52:30 Copycats, Competition, and Patience 53:59 Life After a Successful Exit 55:40 Why Being an Outsider Can Be an Advantage 58:51 Protecting Customer Data and Privacy 59:55 The Negotiation Trick Nobody Talks About 01:01:59 Building Win-Win-Win Partnerships 01:04:05 Why Many SaaS Companies Aren't Enterprise Ready 01:06:53 Work-Life Boundaries as a Founder 01:09:41 Not Every Fire Is an Emergency 01:13:08 Advice for Technical Founders 01:15:14 The Marketing Touchpoints Most Founders Ignore 01:18:18 Final Thoughts CONNECT WITH ELIZABETH DODSON Elizabeth Dodson, Co-Founder of HomeZada LinkedIn: https://www.linkedin.com/in/edodson/ [https://www.linkedin.com/in/edodson/] HomeZada: https://www.homezada.com/ [https://www.homezada.com/] CONNECT WITH MICHAEL J. THOMAS LinkedIn: https://www.linkedin.com/in/realmjt-in/ [https://www.linkedin.com/in/realmjt-in/] STUCK WHERE YOU ARE WITH YOUR TECH OR SOFTWARE PRODUCT? Michael and the team at DARWIN™ Works help SaaS and B2B technology companies create clarity, sharpen their positioning, and drive growth. Find out more: https://www.darwinworks.com [https://www.darwinworks.com/] LEARN MORE ABOUT THE PODCAST Official Website: https://www.iwonpodcast.com [https://www.iwonpodcast.com/]

Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7

This iwon podcast episode revolves around the entrepreneurial journey of Tolu Salami, the award-winning founder of LetPlant. He's an ex Google and Accenture employee with an innovative solution to plant care, combining software and hardware. This discussion dives into many of the challenges faced by founders and highlights the stark reality that only 1 in 200 entrepreneurs succeed, emphasizing the necessity for clarity in problem-solving. Tolu shares his personal experiences, including the pivotal moment that inspired him to create LetPlant after struggling to keep his own plants alive. He talks about the importance of validating ideas through customer engagement, suggesting that aspiring founders should not hesitate to seek feedback before fully developing their products. The episode serves as an invaluable resource for those interested in starting their own business, improving their current one and is a tactical entrepreneurship masterclass, offering insights into perseverance, the significance of understanding market needs, and the role of effective communication in achieving success. In this enlightening podcast episode, Tolu's personal entrepreneurial journey serves as a springboard for a broader discussion on the intersection of technology and sustainable living, as Tolu recounts how he discovered a community of individuals grappling with similar challenges through platforms like Reddit. This discovery not only validated his personal frustration but also illuminated the market gap that LetPlant seeks to fill by leveraging technology to assist users in maintaining their plants. The dialogue further explores the critical importance of validating business ideas before embarking on product development. Tolu highlights the importance (and tactics) to engage with potential customers to gather insights and understanding their needs, a practice he believes is crucial for any aspiring entrepreneur. He cautions against the common misstep of building a product in isolation, advocating instead for a strategy rooted in customer feedback and iterative design. The episode also touches upon the challenges Tolu faced in securing partnerships, particularly with Morrisons, illustrating the resilience required to navigate the competitive landscape of entrepreneurship. In conclusion, this episode serves as a rich tapestry of insights into the entrepreneurial process, emphasizing the need for authenticity, customer engagement, and the willingness to iterate based on feedback. Tolu's journey is a testament to the power of turning personal challenges into innovative solutions, inspiring listeners to cultivate their entrepreneurial spirits with a focus on real-world problem-solving and community-driven approaches. Takeaways: * The podcast aims to unite founders who are innovating compelling solutions to complex problems. * Tolu's venture, Letplant, addresses the prevalent issue of plant care through innovative technology. * Validation of a business idea should stem from genuine customer interactions and feedback, not assumptions. * The entrepreneurial journey is fraught with rejections, but perseverance is crucial to achieving success. Links referenced in this episode: * letplant [https://letplant] * reddit [https://reddit] * henleybusinessangels [https://henleybusinessangels] * pitchuk [https://pitchuk] Companies mentioned in this episode: * letplant * Google * Morrisons * Henley Business Angels * Bootcare * Accenture ENJOYED THIS EPISODE? If you found this conversation valuable, follow the show so you don’t miss future episodes with founders and growth leaders building in SaaS and tech. Leaving a 5-star review on Apple Podcasts or Spotify helps more aspiring entrepreneurs and founders in the trenches right now to discover the show. And, it supports the growth of the IWON™ community. ABOUT THE HOST Michael J. Thomas is a marketing strategist and Cambridge-accredited coach. He founded DARWIN™ Works Marketing in 2011, helping SaaS and tech companies overcome growth hurdles and build sustainable momentum. Learn more about Michael and DARWIN™ here: https://darwinworks.com [https://darwinworks.com] ABOUT IWON™ IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company. * Find out more about the podcast: https://iwonpodcast.com [https://iwonpodcast.com] * Interested in being a guest? https://iwonpodcast.com/guests/ [https://iwonpodcast.com/guests/] * Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ [https://iwonpodcast.com/sponsors/] Michael J Thomas Copyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd.

From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6

Sarah Eggleston's journey from her two-decade tenure at IBM to the establishment of her own startup encapsulates the multifaceted challenges and triumphs inherent in the entrepreneurial landscape. In our conversation, she articulates the harsh reality that merely building a product does not guarantee its success; potential customers must be aware of its value and relevance to their needs. Throughout the discussion, we explore the nuances of transitioning from corporate life to entrepreneurship, highlighting the importance of understanding consumer pain points and the necessity of proactive engagement with potential users before investing resources into product development. Sarah's insights serve as a clarion call for aspiring founders, emphasizing that fear should not deter one from pursuing their ambitions. Ultimately, the episode underscores the importance of community engagement and the iterative process of refining one's vision based on real-world feedback. Takeaways: * Sarah Eggleston emphasizes that merely building a product does not guarantee its success; effective marketing is essential. * The journey from corporate life to entrepreneurship involves significant challenges and requires resilience and adaptability. * Networking and engaging with potential customers can provide invaluable insights before committing to product development. * Successful founders often begin their ventures while still employed, balancing their time and resources effectively. * Inclusivity in technology and software development is crucial for opening pathways for diverse talent across industries. * Understanding the needs of customers and validating ideas through conversations is paramount for any aspiring entrepreneur. Companies mentioned in this episode: * IBM * fflow * Treehouse ENJOYED THIS EPISODE? If you found this conversation valuable, follow the show so you don’t miss future episodes with founders and growth leaders building in SaaS and tech. Leaving a 5-star review on Apple Podcasts or Spotify helps more aspiring entrepreneurs and founders in the trenches right now to discover the show. And, it supports the growth of the IWON™ community. ABOUT THE HOST Michael J. Thomas is a marketing strategist and Cambridge-accredited coach. He founded DARWIN™ Works Marketing in 2011, helping SaaS and tech companies overcome growth hurdles and build sustainable momentum. Learn more about Michael and DARWIN™ here: https://darwinworks.com [https://darwinworks.com] ABOUT IWON™ PODCAST IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company. * Find out more about the podcast: https://iwonpodcast.com [https://iwonpodcast.com] * Interested in being a guest? https://iwonpodcast.com/guests/ [https://iwonpodcast.com/guests/] * Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ [https://iwonpodcast.com/sponsors/] Michael J Thomas Copyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd.

Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5

SUMMARY OF THIS EPISODE In this conversation, Scott Truitt shares his journey from a comfortable career in enterprise software to pursuing his passion for music through his start-up, Sawtooth. He discusses the challenges of the music industry, the importance of artist compensation, and the need for a transparent platform that connects artists directly with their fans. Scott emphasizes the significance of embracing uncertainty, recognizing patterns in business, and balancing passion with financial realities. He believes in creating hope while defining reality, and he aims to build a music platform that prioritizes artists and their connection with listeners. WHAT WE DISCUSS (TAKEAWAYS FOR FOUNDERS/CEOS) * Scott's journey began in the late 90s, rooted in a passion for music. * He transitioned from enterprise software to music entrepreneurship. * The idea for Sawtooth emerged from a desire to support artists fairly. * Scott emphasizes the importance of community and connection in music. * He faced scepticism from industry veterans but remained determined. * Embracing uncertainty is crucial for entrepreneurs. * Pattern recognition helps identify opportunities in business. * Scott aims to create a transparent music platform for artists and fans. * The music industry is risk-averse and conservative, making change challenging. * Scott believes in the importance of honoring one's passion and purpose. CHAPTERS 00:00 Introduction to Scott Truitt and Sawtooth vs Spotify 01:26 The Journey Begins: Passion for Music 04:46 The Evolution of an Idea 10:23 The Call to Action: Leaving Comfort for Passion 15:26 Navigating Uncertainty in Entrepreneurship 21:58 Taking on Spotify: The Vision Behind Foreplay 29:47 Balancing Hope and Reality in Business 32:40 The Journey of Belief and Passion 34:08 Embracing Failure as Experience 36:33 Pattern Recognition in Business 41:24 Building a Community Around Music 45:16 The Economics of Music Consumption 48:17 Navigating the Music Industry's Challenges 52:26 Creating a Sustainable Business Model 01:00:26 The Future of Music and Ownership KEYWORDS Scott Truitt, Foreplay, music industry, entrepreneurship, Spotify, artist compensation, music platform, business challenges, pattern recognition, transparency, iwon podcast, Michael J Thomas, founder podcast, business podcast, real, authentic ENJOYED THIS EPISODE? If you found this conversation valuable, follow the show so you don’t miss future episodes with founders and growth leaders building in SaaS and tech. Leaving a 5-star review on Apple Podcasts or Spotify helps more aspiring entrepreneurs and founders in the trenches right now to discover the show. And, it supports the growth of the IWON™ community. ABOUT THE HOST Michael J. Thomas is a marketing strategist and Cambridge-accredited coach. He founded DARWIN™ Works Marketing in 2011, helping SaaS and tech companies overcome growth hurdles and build sustainable momentum. Learn more about Michael and DARWIN™ here: https://darwinworks.com [https://darwinworks.com] ABOUT IWON™ IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company. * Find out more about the podcast: https://iwonpodcast.com [https://iwonpodcast.com] * Interested in being a guest? https://iwonpodcast.com/guests/ [https://iwonpodcast.com/guests/] * Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ [https://iwonpodcast.com/sponsors/] Michael J Thomas Copyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd. Companies mentioned in this episode: * Spotify * Warp Records * Napster * Kleiner Perkins * Heroku * Instagram